


Feeling Wanted

by Dream_tempo



Category: Supernatural
Genre: Crossdressing Kink, M/M
Language: English
Status: Completed
Published: 2012-08-20
Updated: 2012-08-20
Packaged: 2017-11-12 12:37:13
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,885
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/491106
Author URL: https://archiveofourown.org/users/Dream_tempo/pseuds/Dream_tempo
Summary: <blockquote class="userstuff">
              <p>Dean likes to dress in women's clothing because he likes the way it makes him feel. Though he does look pretty fine in them too.</p>
            </blockquote>





	Feeling Wanted

**Author's Note:**

> Written for dc_summerlovin over on LJ but more specifically dontbitethesun who wanted _"Dean as a drag queen (AU) - it starts when Rhonda Hurley persuades him to try on her silk panties."_ I don't even really know what this is, but I was super proud of myself for getting it done on time since I forgot I was going on vacation the week all this was going down. :P Cuz I'm pro like that. Anyways! I hope y'all enjoy and please comment!!! :D

It started with a simple pair of silk panties.

He'd never intended it to go any further than that- in fact he'd been pretty damn skeptical about trying on the skimpy undergarments in the first place. But Rhonda Hurley was a helluva catch and he was always game for trying something new in the name of sexual gratification. So he'd slipped them on with a wry, teasing smile that slowly grew into a confused, satisfied frown.

They were tight, but also.... Soft. They weren't cut with a man's equipment in mind, but that somehow made it all the better. They were snug, accented all the right things, and left just enough up to the imagination. 

After that, he was hooked. He'd stolen that pair from Rhonda under the guise of a trophy, but every so often when Sam was out and he'd had some time to himself, he'd lock up the doors, strip down, and put them back on. It wasn't always sexual, though over the years the black silk had accrued its fair share of stains. Sometimes he just liked the way they felt, the way they made him feel.

The branching out process was inevitable and he'd known it from the start, even if he chose to ignore it. He'd reasoned with himself that the pair he kept neatly folded and tucked away at the bottom of his duffel were getting a little stretched out, a little worn, they weren’t really his size. So he'd made his way into a lingerie store and with only minimal embarrassment, but a fair share of phone numbers, he'd walked out with a pair of green lace panties.

Then came the black mini-skirt, a tube of guyliner here and there, on one occasion a stick of pale pink lipstick (the red had made him look like a clown, the orange an alien, and the mauve a hooker; an upscale hooker, but still). He'd found places that actually catered to men, though most were for full-scale drag queens. He didn't really consider himself a drag queen yet- wigs drove him insane and heels turned out to be just short of suicide. He just had an.... interest. Something of a kink. And if at some point he'd ended up with a corset, well that just meant he had quality taste.

He'd never shared this with anyone- not Sam, not Cas, not even the dirtiest one night stands he'd ever had. He wasn't sure they'd understand, wasn't even sure that he really did. Dressing up like this didn't mean he acted feminine, didn't mean he wanted others to address him as a woman, like other men did. He just liked the way he looked, the way he felt, the way he imagined he'd drive every man and woman that laid eyes on him crazy.

Tonight Sam was out having a much needed "conjugal visit" with the woman who'd been flirting with him across the bar and Dean had some mild stress relief planned for himself too. Tonight was gonna be the night. Tonight he was finally gonna feel those hungry stares on his back, validate this sense of empowerment he got from the materials he so closely guarded from everyone. So he'd ushered his little brother out of the room with perhaps a little more gusto than was necessary and then immediately went rifling through his bags. In a place like this the night life stayed out at least till five, but it was already nearly one and he wasn't about to miss out on the opportunity.

First came a pair of silk ungergarments he'd bought that looked black in the dim, grungy hotel room, but which actually shimmered an olive green under the light, and over those the aforementioned mini skirt. Leggings and tights were just downright irritable with the amount of hair on his legs, but that wasn't something he wanted gone. On the occasion that he had fallen into bed with some guy that he just couldn't pass up, he'd always loved the rough scratch of stubble, the friction a little bit of fur provided, the hard lines and rough demeanor. When he slept with a man, he wanted the experience to be wholly different. So instead he zipped up a killer pair of knee high boots to cap off his lower half.

He kept it simple for his torso - a white button down with lace through the chest. His rings and wrist bands fit well enough with everything that he didn’t have to leave them in the room, but he tucked the frankly off putting amulet Sam had given him into the neck of the shirt. Now he only had one part left before he was ready, and he'd be lying if he didn't say that the last part was his favorite, but it wasn't something he liked to admit.

Standing in front of the water stained mirror of the bathroom he meticulously started to outline his eyelids with jet black eyeliner, taking his time to make sure the coating was even for both eyes. After that a layer of lime green eye shadow that had glowing gold and orange glitters which set his eyes aglow and took far too long to learn how to apply correctly. But the pièce de résistance is the dusky pink lipstick that's so smooth and languid it's as though it pours out of the tube to stain his lips. Content with everything he steps back to take a final look and can't help the full-blown grin that hijacks his features. He. Is. Fine. He lets out a low whistle and can't quite stop himself from thinking he'd screw himself if he were able. Scientists needed to perfect cloning already because he'd order a few of himself and be set for life.

He grabs a wad of cash out of his wallet and is in the process of stuffing it in the waistband of his panties seeing as how he didn't have the convenient cleavage pocket women do when he hears the familiar flutter of wings and the bottom of his stomach drops out. "Shit."

"Dean?"

He only allows himself a moment to gather the courage to turn around before fixing an irritated expression on and spinning on the toe of his boot. "What do you need Cas? I'm a little bit busy." He emphasizes by cocking a hip and gesturing nonchalantly at his clothes.

"Clearly." Cas just raises an eyebrow and takes a quick once over before licking his lips and going to sit on the edge of one of the beds. "I suppose I can just wait here until you're finished."

The whole thing catches Dean a little off guard and he reels for a second before going to sit beside his angel. "Why aren't you freaking out about this?" He doesn't know why he questions the break he's been given- maybe he just knows better than to trust when things come easy, maybe it’s just in his nature to look a gift horse in the mouth, but suddenly he just has to know.

Castiel looks at him like he always does- like Dean’s very existence is beyond puzzling. “All humans like to feel wanted. This, I know for sure.”

All he can do in response is shake his head in amazement- it would be that strangely simply for the angel. He's about to tell Cas off, make some snarky comment and hopefully go on with this night as planned- though the mood might be ruined if he thinks about it as he should- when the other man continues on. "You know you really are quite beautiful Dean." There's no lie in the words, no hint of condescension or patronization, just honest opinion. It's so fresh, new, and exactly what he needed, even if he didn't know it at the time.

"Thanks Cas." his voice comes out a little huskier than intended and he makes damn sure to take control of the wet starting to form behind his eyes. This damn make-up was expensive and he'd sooner go back to hell than waste the rather large amount he'd put on tonight. "I-ah really should go, don't wanna put all this effort to waste, y'know?" He stands up to leave, hopefully determined to forget this whole exchange with some free drinks and a good hard fuck with whatever poor sucker took him home.

"You... don't have to. Leave that is." Castiel is looking determinedly at the floor- finding a sudden fascination in the pattern of the dingy carpet- and his hands are twitching nervously in his lap.

"What did you say?" Dean really wants to pretend that it's fear and not excitement currently coursing through his veins, but not even he could pull of a lie that big. Castiel looks at him with an innocence that would fool all but the most trained eye, but Dean's fairly certain that he's pretty well-versed in Cas' special brand of minute body language. The other man is starting to get a flush across his cheeks and the confused shuffling of his feet is very familiar to every adolescent boy that's gotten a surprise boner in a location they wish they hadn't.

"I... am never too pleased to leave your company in such a brisk manner." The obvious hedging makes Dean smirk and gives him a bit more of a foot hold as to how to act in this situation. He worries at his bottom lip, making sure to be harsh enough to make the flesh plump and swell. When Cas watches with an avid fascination before tightly squeezing his knees together and checking the position of his trench coat, Dean can't help but grin at the fact that his lip isn't the only swelling flesh. He's always loved making the angels squirm, but this particular one in this particular situation was something he had only ever hoped for in his most sordid dreams.

"Well gosh Cas, I don't wanna make you uncomfortable, maybe I should take off this get-up." Dean starts to unzip the waist of his black miniskirt when Cas makes a choking noise and reaches out toward him before the angel can think better. Immediately Cas' eyes widen in horror and he freezes, perhaps thinking Dean might forget he's there if he prays for it hard enough. It’ll be a cold day in hell when Dean Winchester passes up an opportunity like this, and though the thought of him and Cas still makes his throat close up a little in anxiety, he wants this. And what Dean wants, he takes.

It only takes one long stride to reach Cas, and then Dean is hiking up his skirt and lowering himself into the angel’s lap. A breathy, “Dean…” is all he gets, but the blue in Castiel’s eyes has almost been completely engulfed and in this position there’s no denying their twin erections. Dean twines his hands behind Cas’ head before pulling the both of them down to lay on the bed. He maneuvers Castiel on top, but wraps his legs around the other man’s waist and uses them to pull Cas’ groin up and into his skirt. The two of them groan in unison and Dean knows this night is gonna turn out to be so much more than he planned…


End file.
